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Miley Stewart has the best of both worlds, girl next door by day and famous teen pop sensation Hannah Montana by night and the best part is nobody knows! That is until Miley's best friend, Lilly Truscott, sneaks into Hannah Montana's dressing room and discovers her secret. Together the two friends lead a normal teen life all the while protecting Miley's secret identity.
Miley worries that Oliver's obsession with Hannah Montana has gone too far and decides to do something to cure him. Aware that he has a strong aversion to people who chomp their gum, she puts on her Hannah disguise and Lilly arranges a coincidental beachfront meeting with Oliver. When Oliver discovers that Hannah Montana chomps her gum he is still not cured of his obsession so Miley finally resorts to revealing her true identity. Jackson buys a used car and panics when he learns from Cooper that
Miley and Jackson sneak out of the house to check out a movie and inadvertently spot Robby at the same theatre on a date. Determined to learn more about the woman, Miley dresses up as Hannah Montana and convinces Jackson to accompany her to the real estate agency where she works. There, they must quickly retreat and hide in a nearby closet when Robby arrives. In a heartfelt moment, Miley confesses that she misses her mom as does Robby.
Learning that her new beau, Josh, despises Hannah unsettles Miley; Josh agrees to go a concert if Miley goes with him.
Hannah is invited to the birthday party of a pop star and worries that Lilly might embarrass her too bad to take her. So she lies and says the party is cancelled but when "Hannah" arrives at the party (which she was assured would be paparazzi-free), a photographer takes her picture. Horrified that Lilly might see the picture in the tabloids, Miley tries to keep Lilly from seeing the news. Rico dupes Jackson into letting a beauty school girl, Nina, experiment with his hair.
Hannah performs for the Queen of England; in town for a surprise visit, Miley's grandmother helps Jackson prepare for his big match.
Robby goes astray when picking a gift for Miley, who winds up having to wear a tacky sweater to her birthday party.
Miley and Lilly want to spend more time together so they try out for cheerleader only this time, Lilly lands in the limelight with a spot on the squad while Miley is in the background as Mascot. Ironically, the coach tells Miley she doesn't have what it takes to perform in front of a crowd and Miley is humbled to learn what it's like to be on the sidelines. At home, Robby and Jackson attempt to fix a broken sink.
Miley, Lilly and Oliver get revenge on Amber and Ashley during a camping trip, but what they do rebounds on Miley in her Hannah Montana identity. Meanwhile, Jackson and Robbie have a mouse problem.
Oliver is upset when he overhears Miley saying she doesn't want him to help with the drama class performance because of his stage fright. Then she gets nervous and forgets the words to the national anthem.
Miley and Lilly decide to play matchmaker for Hannah Montana's fan Becca, who fancies Oliver. The couple do get together, but Oliver is not impressed with her snooping.
Robbie misses performing himself, now that he is just his daughter Hannah's manager. He agrees to do a five night stint at an out of town club, with disastrous consequences.
Lilly's dog eats her contact lenses and she is forced to wear her old, big, black-framed glasses. Miley tells her not to be vain, but then Miley herself complains when a spot is added to her face on a poster of a skincare ad.
A new pupil turns out to be Jake Ryan, who stars in a hit TV show. Most people are thrilled and he gets lots of attention, which makes Miley jealous.
Miley declines Jake's invitation to the school dance but later changes her mind and finds out he has asked Lilly.
Miley, Lilly and Miley's godmother, from Tennessee, must retrieve a videotape telling of Miley's feelings for Jake.
It's Halloween but the only thing frightening Hannah is her cousin Luann, who is threatening to tell the world that Miley and Hannah are the same person.
Miley is determined to make Jake jealous, but her plan backfires when the boy she chooses embarrassingly turns out to be very young. However, Jake does ask her out again in four months.
Miley, Lilly and Oliver attempt to raise the most money for a school fundraiser; Jackson wants to beat Robbie at pingpong.
Miley goes on a spending spree and is afraid Robbie will find out, so Jackson plans to auction off some of Hannah's old clothes.
A sneaky photographer takes a picture of Hannah and Jackson, leading everyone to believe they are an item. Hannah wants to own up, but Jackson's enjoying the limelight.
Hannah gets her brother sacked from his beach bar job, so she's forced to make him her assistant, but that proves a disaster when he's always getting things wrong.
Roxy attends Sea View Middle School as a new tween student in order to protect Miley from the new school bully, the Cracker. Unable to take Roxy’s interference with her school and social life, Miley finally does the right thing and gets the principal involved to help solve the problem. Robby & Jackson get stuck in the snow when attempting to take a weekend fishing trip and meet a lonely inn keeper and his ventriloquist dummy.
When Miley's school rival, Amber lands a spot on the Singing with the Stars Competition featuring Hannah Montana, Miley, Lilly and Oliver see it as an opportunity to finally embarrass her once and for all. But Miley's conscience gets the better of her and in the end she allows Hannah's performance to be sabotaged instead of Amber's. Meanwhile, Jackson and Robby try to solve the problem of their next door neighbor, Mr. Dontzig's barking dog.
Miley commits to endorse a new fragrance but ultimately can't stand the smell of it and decides to back out of the deal in the name of honesty. Oliver videotapes Jackson's audition efforts to land a role on a popular kids reality series about survival.
When Jackson tires of driving Miley around and attending to his little sister's overall needs in general, Miley challenges that if she were the older sibling, she'd willingly do for her sibling. Jackson then puts her to the test by arranging for Miley to babysit their neighbor, Mr. Dontzig's bratty niece. Meanwhile, Roxy performs her bizarre home remedies to nurse Robby back from a cold.